The Stacking Benjamins Show

Ever wish you had a second chance with your money? Billy B. hoped he'd get one. After being convicted and sent to prison after the death of his friend, Billy went through some serious soul searching, and the end result of that is on display on today's show. Not taking any opportunity for granted, working hard to find solid financial (and life) footing, and the value of surrounding yourself with good friends and mentors are just three of many themes we'll talk about in this fantastic discussion with Billy (who now also blogs at WealthWellDone.com). We originally aired this show in 2018, but the lessons Billy learned are truly timeless. Read the rest of the original show notes below:In our headlines segment, a new software program means that some of your advisors may be expendable….or maybe not. We’ll discuss the hot topic of humans versus AI on today’s show. Plus, Warren Buffet just wrote his annual letter to investors. What are some of the takeaways? One publication listed their favorites and we’ll review and discuss them. As always, Mr. Buffet doesn’t fail to use the English language as a weapon while talking about investing, value, and evaluating risk.We’ll of course have more from the world of financial planning, throw out the Haven Life line to lucky listener Luke, who wonders about investing to beat inflation without taking too much risk. For a five year goal, what investment works best? Are stocks too risky? Should he use junk bonds? We’ll shine a light on that topic (and maybe one we can’t talk about here), as well. We also answer a letter from Jon, who asks about asset allocation. What is a great way to manage your money and diversify correctly? You’ll have to listen to find out!Of course, we’ll still score with some of Doug’s delightful trivia, and more. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Got debt? We have a solution. Or rather, our guest, Jenni Zepol, does. Every eight weeks we look back through our collection and play some of our favorite interviews, and this one is no exception. No gimmicks or get rich-quick schemes - Jenni shared her strategy and goals on how she paid down her debt in less than a year and they just may work for you too.Here's our original show notes:We LOVE success stories, and today we're talking to one woman with a great one. She set out to pay off over $18,000 of debt in a single year. But what happened? She actually did it in just over half that time: seven months. Sounds good? We thought so too, so we called up Jenni Zepol to see just how she did it. The great news? Many of you may be able to follow her tactics and do it also.Plus, in our headlines segment one whistleblower claims she was fired for raising red flags about her employer's alternative investment sales. While we're not going to set out to prove or disprove her claims, we will draw a point on why it's important to make sure your advisor is always acting as a fiduciary while helping you handle your finances. And in our second headline, one Florida teacher quit his job to become a 6-figure earning personal shopper. Any lessons we can learn there? Absolutely.We'll also have time to answer a listener letter, and don't you worry, we'll also dish out a dose of Doug's trivia. Learn more about your ad choices. Visit podcastchoices.com/adchoices

"You'll spend more time searching than watching" would be an honest slogan for which company? If you said… well, let's not spoil every element of the show before it starts.During today's special game show we ask our contributors to guess which companies our "honest" slogans belong to. It's a lot of fun, and one contributor has a bit of a hard time marking their place on their board. Our contributors joining our round table this week are Stacy Johnson from the Money with Stacy Johnson podcast, Len Penzo from the LenPenzo.com blog, and Paula Pant from the Afford Anything podcast.After we wrap up our gameshow Joe sits down with the founder of Element, a new company designed to help personal finance creators answer questions from their audience. During their discussion Orban Oz shares how he discovered a startling statistic during his time building up a digital bank: personal finance creators are being asked questions all the time. That's where Element comes in. The platform sets out to make creators more accessible to their audience, and better response times. Today we dive into how it all works.We finish today's show with a question from Michael, who's wondering if he's too conservative in his portfolio. Michael is 58 and his portfolio is 60% stocks and 40% bonds. He also has a pension with 100% survivorship benefits for his spouse. Michael also tell us he doesn't include the pension in portfolio allocation as fixed income.He asks us two questions: is he being too conservative not including his pension in his calculations, and two, how much (if any), of their 1.4 million 401k should they convert into a Roth in retirement?Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

It's a bold statement, and one financial coach Rachel Rodgers wholeheartedly believes. After adapting her coaching business last year to the difficult circumstances we were all facing, Rachel not only survived but thrived. She saw her company turn its first million-dollar month not long after. Today Rachel shares how you can get to millionaire status: a change in your mindset, enforced boundaries, and purposeful changes in your community can lead to huge financial improvements in your life.In our headlines, and to no one's surprise, half the country is waiting for a vacation. While airlines can handle the traffic, car rental companies can't. After selling off fleets to stay afloat, there flat out aren't enough cars to go around anymore. In Hawaii, tourists have taken to using U-Hauls to get around. Are YOU planning a vacation soon? We share what you need to be doing (like yesterday) to make sure you're protected during our first headline.Looking for headlines on saving money? We have that too.Ever hear about tax-loss harvesting? If you've ever made bad stock-buying decisions at two in the morning despite all of our warnings, tax loss harvesting is your new best friend. This isn't the whole bit, but basically, it lets you use the losses on your stocks to lower the bottom line on the taxes of the stocks that actually performed well. Win-win, right? Or as most of a win as you can get in the situation. Joe and OG don't stop there, after giving the breakdown on tax-loss harvesting the guys also share tips on reallocating, understanding the differences between ETFs and Mutual Funds, and more.We finish today's show with a question from an anonymous listener who's wondering how to invest all of his extra cash. Anon has regular W2 income and about $20,000 in self-employment income that they're not sure what to do with. Ideas? The guys give a breadth of things to consider including opening up a SEP IRA, talking to a CPA, different considerations for if our caller is running a side business with frequent income, contribution and tax implications, and more. Plus, we'll finish our answer with some tax-savings advice that's especially helpful for freelancers.Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Susan, Linda, Nina, and Cokie--four women we know by first name--were collectively much of the "voice" of NPR, bringing the fledgling network into millions of homes during an era when woman weren't even expected to report news, let alone host shows control what topics were discussed. Today we hear a few of their stories from master researcher and storyteller Lisa Napoli, journalist and the author of Ray & Joan among others. She'll share how you too can achieve your goals and create your dream job - even if it doesn't yet exist.While these stories are downright interesting on their own, they also serve as great examples of achieving your goals, not limiting yourself, and learning how to thrive in environments where you're not expected to win.During our headlines we tackle an issue most of the world's procrastinators have faced since working from home: keeping the ball rolling on your work. Studies show that the last year has been difficult for most, and we still have many lessons to learn about maximizing productivity and staying active when we're sometimes only feet from our bed (or the XBox/kids/fire pit/whatever). We've had experience figuring out how to keep productivity and workflow up, and we don't mind passing that advice on to you, along with some help from a great piece from the Wall Street Journal.In our second piece, should you trust all of the new, up-and-coming "buy now, pay later" services? While you should always use some judgment while considering any purchases, there's a bigger question to answer here: WHY use these services? If you're already financially responsible enough to use credit, there are plenty of great credit card rewards programs to utilize instead. If you're not responsible... well we're back at square one, aren't we? We'll discuss the "why?" with these services and detail how they work.We finish today's show with a question on HSA investing from Stephen who asks: should he pay for medical expenses out of pocket to allow his HSA contributions to grow interest? Similar to our "buy now, pay later" thoughts, it's not that our answer is necessarily no for Stephen, there are so many things that can go wrong here we have to take a moment to air some concerns.Of course, there's always time for Doug and his trivia.Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Where do you turn when being poor has you exhausted? When you feel like you just can't think about ways to make money any longer? On a bigger scale, what's the secret to breaking out of poverty and the cycle of always being in debt? While we won't promise to solve the world's longest-running crisis in one podcast, our contributors all share their experiences and thoughts about working to overcome poverty. They share how they endured their own individual situations, and how they (and you) can plan and work towards getting out of a dark hole yourself. There aren't any quick fixes, but we do offer solid financial strategies that'll move you past the paycheck to paycheck lifestyle.How about some "free" Bitcoin? During our Friday Fintech segment we'll talk to Quontic Bank founder-CEO Steve Schnall. The digital bank, which offers a Bitcoin "cash-back" rewards card, also handles non-traditional mortgages to help under-served people who need it most. You'll especially want to listen to this one if you're in the hospitality business or any other industry with hard to document income.We end the show with a question from Nick. He tells us he's got an offer for a 2% cash back card. Nick is excited about using the card, but worried about his credit utilization rate. He's heard that 30% credit utilization is as high as he can go before his credit is negatively affected. Nick also asks if his credit is hit right away, or only when his statement is sent out. Our contributors share a full round of their thoughts before calling it quits for the weekend.Of course, Doug has some airtime for his trivia game-show. Learn more about your ad choices. Visit podcastchoices.com/adchoices

What separates you from everyone else? What gives you a competitive edge? According to William Green, who's interviewed hundreds of the richest investors on the planet, most of us don't have a competitive investing edge. But there's good news: that's okay, as long as you know who or what you're emulating. Today he'll pull on interviews from his new book, Richer, Wiser Happier, How the World's Greatest Investors Win in Markets and Life, to share how we can overcome our disadvantages and turn them into strengths. He'll also share some of the often-overlooked personal sides of a few investing magnates that we don't often get to see. You'll hear human stories about Jack Bogle and Warren Buffett, among others.Keeping (in)famous people in mind, we'll also cover Bernie Madoff - and scams - during our headlines. The mastermind behind the largest Ponzi scheme to date, Madoff often served as a stark reminder of the things that can happen when investors turn over their cash to unethical advisors. We'll also share the latest developments of the advisor who ran away with millions of his clients' dollars, and a few scam experiences of our own.Plus, if you're still waiting to file your 2017 taxes (I'm being serious), you only have limited time before Uncle Sam claims your cash for himself. I understand procrastination as much as the next wait-until-the-night-before person, but this is something you'll want to do sooner rather than later.During our Haven Life line segment, we help out James, who has dreams of becoming a financial planner. His bigger issue? He already has student loan debt from another degree. James asks: can he become an advisor with no relevant degree or experience? Joe and OG give James all the information he needs to get started on his path.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you take care of your money? Is it dollar by dollar? Or do you swipe plastic (like we used to), hoping that the math in your head has worked out? Today we'll help you take control with a discussion about creating a budget meeting, changing your money mindset, and gaining the confidence you need to drive your goals. It's a powerful show and we're excited for you to hear it.Featured Guest: Catherine AlfordCatherine Alford shares tips to help you take control of your life by utilizing the skills you already use every day. Cat's new book, Mom's Got Money: a millennial mom's guide to managing money like a boss has strategies, tactics, and ideas anyone can use. From money meetings to making small changes in your decisions leading to big habit and money improvements, there's plenty of options right within reach.Do You Really Own Your Virtual Investments?We'll also dive into the world of NFTs. Let's assume you're fully funding your other retirement vehicles and you're interested in putting some fun money into a fun NFT spot like NBA Top Shot. (Which is a new blockchain virtual sports card marketplace... thing).You actually made a nice profit and want to cash out... and here comes the headache. You realize it'll take months for your gains to become liquid, but you need cash yesterday. What now?It doesn't matter if you're investing in a Traditional or Roth IRA, annuities, virtual card trading marketplaces, or anything else - always make sure you understand what you're throwing your hard-earned Benjamins in. We explain more during our headlines.Vacationing Next Year? Buy Now!In our own little version of market timing, all signs point to "recoup lost revenue" when it comes to the airlines industry. If you're sure you'll travel next year, it might be good sense to buy that ticket now. We discuss travel, airlines, and more during our second piece.The Haven Life Line: Terrible 401k Options? Here's What To DoKyle calls in and tells us he has terrible 401k options. His workplace plan offers one index fund and a host of high expense ratio plans. While he invests some cash for the company match, most of his contributions go towards his IRA. Kyle asks: what should he do in this situation? How can he get his workplace to offer better plans?As always, we'll save some airtime for Doug's trivia.Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

You've saved and invested diligently for years and you're now sitting on a fat stack of Benjamins. When's the right time to say f*** it and start spending cash like there's no tomorrow? Today our contributors share their big spender to saver money stories and give their thoughts on retiring WAY early... on less than a million dollars. It's not always about the bottom dollar, but also lost potential income (and raises) if you need to return to work years down the road, lost marketability as your skills age, and outdated professional networks as your co-workers move on to other opportunities.Joining us on the roundtable this week is Diania Merriam, founder of the FIRE-Movement inspired EconoME Conference, Len Penzo from the LenPenzo.com blog, and OG from our own podcast.Friday Fintech: Health and Wellness Expert Angelo Poli from MetPro.coAfter our contributors finish swapping money stories, Joe sits down with health and wellness expert Angelo Poli from MetPro.co. With summer right around the corner, we polled our Stacker community for all the health and exercise questions they've been dying to get answered. From questions on aging metabolisms to intermittent fasting, and of course, time-efficient (and free) workouts even the busiest Stackers can do at home... Angelo covers it all and then some.Listener Voicemail: HSA Horror Stories?Our anonymous caller, who we refer to as Sal, calls in with some HSA questions. For years he was told he only needed the Explanation of Benefits form (think something like a medical statement) before finding out he actually needed his receipts as well. While this was an easy fix, Sal asks: what other blind spots could he have? What HSA horror stories should he know about - and avoid?As always, Doug has some post-Fintech airtime to deliver his game-show trivia.Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

How do you make money driving for ride sharing companies? Credit card hacking? Churning bank accounts? How do you help your family plan? What's it like to meet with financial advisors? Today members of our community, Alan, Claudia, and Jon are kind enough to share their wisdom and experiences in all of these areas! Plus, we'll also share an important headline about doing your homework before investing, another on helping your community, and more.Of course, we'll also throw out the Haven Life line to a caller with a great question about estate planning. That comes after Doug's trivia and a few of your emails.Enjoy!  Learn more about your ad choices. Visit podcastchoices.com/adchoices